Our invention relates to the preparation of novel acetyl isopropyl tetramethylindan musks, organoleptic uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles, as well as a process for preparing same and novel intermediate therefor.
There has been considerable work performed relating to substances which can be used to impart (or alter, modify or enhance) fragrance to (or in) various consumable materials. These substances are used to diminish the use of natural materials, some of which may be in short supply and to provide more uniform properties in the finished product. Sweet, ambrette seed-like and musky aroma characteristics are particularly desirable for many uses in several types of perfume compositions, colognes and perfumed articles (e.g. solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, perfumed polymers, cosmetic powders and hair preparations).
The production of isochromans, for example, has been shown in the prior art and certain novel isochromans have recently been disclosed as outstanding musk fragrances. Such isochromans especially adapted for perfumery by virtue of their properties have been disclosed in Heeringa and Beets U.S. Pat. No. 3,360,530 issued on December 26, 1967.
Acetyl tetralin musks such as that having the structure: ##STR8## produced according to the reaction: ##STR9## are disclosed in U.S. Pat. Nos. 2,752,404, 2,759,022 and 2,851,501 (commonly termed "Tonalide," for example).
Acetyl indan musk compounds, for example, having the structure: ##STR10## is disclosed in Dutch published application 78 02038 (corresponding to U.S. Pat. No. 4,352,748 issued on Oct. 5, 1982) and commonly termed "Traeseolide."
The Givaudan Corporation of Clifton, New Jersey published in a series of 9 articles in the "Givaudanian" starting with January, 1968, a review article on the "Chemistry of the Aromatic Musks" and in said review article discloses the following compounds with their properties:
TABLE I ______________________________________ Structure of Compound Odor Evaluation ______________________________________ ##STR11## Musky and woody ##STR12## Weak musk odor ##STR13## Odorless ##STR14## Odorless ______________________________________
The Givaudanian articles thus disclose compounds defined according to the generic structure: ##STR15## wherein R is methyl, ethyl, n-propyl and isobutyl but do not disclose compounds defined according to the structures: ##STR16## (wherein R is isopropyl).
Nothing in the prior art discloses the rearrangement reactions: ##STR17## enabling efficient production of the compounds having the structures: ##STR18##
The compounds having the structures: ##STR19## have unexpected, unobvious and advantageous organoleptic properties in perfumery with respect to the other compounds
having the structure: ##STR20## wherein R represents methyl, ethyl, n-propyl and isobutyl.